4.4 Article

An efficient approach to the stereoselective synthesis of 2,6-disubstituted dihydropyrans via stannyl-Prins cyclization

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 4, Pages 678-681

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.11.128

Keywords

vinylstannanes; dihydropyrans; prins cyclization; (-)-centrolobine

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A general method has been developed for the stereoselective construction of 2,6-disubstituted dihydropyrans based on the Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with vinylstannanes. This novel methodology was applied to the enantioselective total synthesis of (-)-centrolobine. (c) 2007 Elsevier Ltd. All rights reserved.

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